Sodium Iodide → HCID 54112049, compound

HRID 2186286Notes

Reaction equation

HRID 2186286 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([O:18]C)[CH:8]=[CH:9][C:10]=1[O:11][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:4])([CH3:3])[CH3:2].[I-].[Na+].C[Si](Cl)(C)C.C(=O)(O)[O-].[Na+]>C(#N)C>[C:1]([C:5]1[CH:6]=[C:7]([OH:18])[CH:8]=[CH:9][C:10]=1[O:11][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 516892Sodium BicarbonateHCID 536448783-t-Butyl-4-trimethylacetoxyanisole

Product 1

HCID 54112049HCID 54112049, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5.00 g of 3-t-butyl-4-trimethylacetoxyanisole was dissolved in 45 ml of acetonitrile and 4.54 g of sodium iodide was added at room temperature under a nitrogen stream and 3.84 ml of trimethylsilyl chloride was further added dropwise. This solution was refluxed for 6 hours, then poured into a saturated aqueous sodium bicarbonate solution and extracted with diethyl ether. The organic layers were washed with saturated brine, dried over anhydrous magnesium sulfate and then concentrated. The concentrate was purified by silica gel column chromatography (in n-hexane containing 17% ethyl acetate) to give 4.50 g of 3-t-butyl-4-trimethylacetoxyphenol as a white solid (yield 95%).

Workup

  1. additionwas further added dropwise
  2. temperatureThis solution was refluxed for 6 hours
  3. extractionextracted with diethyl ether
  4. washThe organic layers were washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe concentrate was purified by silica gel column chromatography (in n-hexane containing 17% ethyl acetate)

Sources & evidence

ORD record
ord-33176a231fb54c6c88f525d5645ad3fc
Source dataset
uspto-grants-2002_06
Patent number
US06403639B1

Reaction notes

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